The second season of the Americantelevision comedy series How I Met Your Mother premiered on September 18, 2006 and concluded on May 14, 2007. It consisted of 22 episodes, each approximately 22 minutes in length. CBS broadcast the first three episodes of the second season on Monday nights at 8:30 pm in the United States, the remaining episodes were broadcast at 8:00pm. The complete second season was released on Region 1 DVD on October 2, 2007. In the United Kingdom it aired via E4 from October 2, 2009 weekdays at 7:30pm.

The gang tries to help Marshall get over Lily. Barney takes him to a strip club, and Ted takes him to a Yankees game. Marshall finds a credit card trail that leads to Lily's hotel in the city, but the guys try to keep him from going to see her.

Barney teaches Marshall how to pick up women. When things start to go sour for an awkward Marshall, Barney steps in and wins the women over... for himself. Lily returns from her art experience. While helping her look for a new apartment, Ted gets sick of hearing about Lily's amazing summer in San Francisco.

When Ted, Robin, and the gang spend the weekend with his parents, Ted is stunned when a family secret that changes things forever is unveiled at brunch. Meanwhile, Marshall and Lily find it difficult to control themselves when they are forced to spend time together with Ted's parents.

After Robin insinuates that Ted's job is boring, Barney sets out to convince his buddy otherwise. As the guys test out the pick-up line, "Ted Mosby, Architect" on the ladies, they realize it really works. But when Robin hears that Ted is parading around town picking up girls, she is hot on his heels to discover the truth.

Robin wants to tell Ted she loves him, but she can't make the leap. Meanwhile, her sister visits and brings her boyfriend, and Robin doesn't react well when her sister says she's ready to lose her virginity.

When Ted is constantly insulted by his former boss, who is now working for him on a project, he is told to fire the man, but he finds that a hard thing to do. Meanwhile, Barney offers Lily a lot of money to paint a nude portrait of him.

The group plans to watch the Super Bowl XLI when they are invited to a funeral on the same evening. They make plans to record the game and to not find out the score before watching it the following day.

After Robin gives Ted grief over keeping all of his gifts from ex-girlfriends, Ted decides it's time to give them all away. However, the tides change when he finds that Robin has been holding on to items as well. Lily forces the whole group to come to her play.

As Ted and Robin hit a new milestone in their relationship, Barney does everything he can to derail their happiness. To do so, Barney steals the rental truck Ted is using for moving day, including all the belongings inside of it.

Lily and Marshall's wedding day arrives, but nothing goes as they had planned. Surprisingly, Barney steps in to save their once-in-a-lifetime moment. Meanwhile, Barney abuses the 'it's for the bride' superpower.